The First time: A Tomboy Liley Prequel
by SilverDragonRanger09
Summary: Alook back at before Miley and Lilly were famous and Miley loosing her virginty


**A/N: What up Tomboy Liley fans it is I the king of Tomboy Liley the often imitated but never duplicated Mr. SDR09 the renegade Dave. Now this story is a prequel and takes place before Miley and the crew were famous and deals with what I find an interesting thing the fact that although that some girl, girl couples have sex some girls will consider themselves still technically virgins because well no ones ever broken their hymen. In this case its Miley who is still a "virgin" and she has decided to give that part of herself to Lilly. So please enjoy this**

Miley paced around the living room area of the two bedroom apartment she shared with her three best friends. Her cover alls she'd worn to work that day hanging at her waist and her cornrows matted and butterflies in her stomach as she dialed her girlfriend of almost four months number. Miley could not believe it had been four months since she had met the beautiful blue eyed blonde that was Lilly Truscott. Lilly seemed to be the answer to her prayers, she was everything anyone could want in a woman. She was attractive fun kind loving and Miley was truly in love with her. Which made the call she was making more nerve racking but at the same time filled her with excitement. '_I can't believe I'm doing this,' _Miley thought as she waited for the person on the other line to pick up.

"_Hey sexy,"_ Lilly said her bubbly voice making Miley melt.

"Hey baby girl what you up to" Miley said trying to conceal the nervousness in her voice.

"_Nothing just economics why something up," _Lilly asked picking up on the tone of Miley's voice. In the four months she'd known the somewhat masculine brunette she'd learn to read her vocal tones and could tell her girlfriends emotions.

"Nothings wrong babe I was just wondering if you'd come over a little later and listen to this new track Dave and me have been working on," Miley said coyly.

"_Um hmm, and I'm suppose to think that's all we're going to do right" _Lilly said knowing full well she was right.

"Well shawty you know I love to lick my Lilly-pop," Miley said in slick voice.

"_Uh huh give me like two hours or so and I'll be over mama," _Lilly said using her nickname for Miley. Lilly had been in love with Miley from the first time they danced together and couldn't wait to see her. She was so fascinated with the would be R & B star and fully supported her dreams, and knew one day that those dreams would come true.

"Okay baby love you," Miley said adding a kiss for emphasis.

"_Love you too Miley,"_ Lilly said as they ended the phone conversation.

"_Oh God please let this go right,_" Miley thought. "_Ok just relax you're Miley Ray you can do anything. Yeah anything but why are you nervous about this,"_ Miley's thoughts trailed on as her roommates walked through the door

"Yo Miles guess who could have a gig at _Dreamz_ Saturday night," David said as he came in taking of his jacket.

"Yeah Davie gave the owner your demo and he's gonna let us open when Mike Jones comes to town Saturday," Mikayla said flopping down onto the couch pulling her girl friend Demi into her lap, "and with my sexy little Dem, Dem as our back up dancer we gonna tear the place up," she continued.

"That's right "pretty boy" ," Demi said kissing Mikayla.

"That's what's up! Now get out," Miley said shocking her friends.

"Damn last time I bring you good news, what's the deal sis,' David asked.

"Yeah we should be celebrating, what gives with the kicking us out" Demi said wanting answer.

"Lilly's coming over," Miley taking off her shoes and socks.

"And ?" David asked grabbing a Snapple bottle from the fridge

"And we're going to you know do stuff," Miley said.

"So nothing we ain't heard before what's the big deal," Mikayla said.

Miley looked a her friends nervously rubbing the back of her neck, carefully thinking of something to say. "Tonight's different Mik," she said.

"Different? Different how Mile," Mikayla raising her eyebrow.

"Look Mik it's just tonight !..... Tonight's the night Mik," Miley said with a slight red blush.

"Oh my god you're god you're still a virgin!" Mikayla said almost dropping Demi on the floor.

"Damn well announce it to everyone in the building!" Miley said as she fell back onto an empty space on the couch.

"Um excuse me straight guy in the room. How the hell is the great Miley Ray still a virgin I mean I've walked in on her and Lilly on the couch like twice and believe me virgins don't what ya'll were doin," David said getting a slightly annoyed looks from the three young women he considered his sisters.

"Dave Miley must we teach you everything. Miley's only still technically virgin because she still has her cherry," Demi said getting an angry look from Miley. "What are you mad about we tell him everything anyway. He's like one of the girls," she continued..

"You know Lovato you really need to learn to shut up sometimes." David said, " Anyway I get kid just let me change really quick then you and Lill can have the place to yourselves," David said walking over to Miley and patting her on the shoulder and walking into Miley's room, to get the clothes he stored in her closet

"So Mile you nervous?" Mikayla asked.

"Yeah I mean I've never anything like this what if I screw it up," Miley said rubbing her temples. "What was it like for you two," she asked, wanting an answer.

"Well Miles I know for me it hurt a little more because someone didn't know how to go slow at first," Mikayla said making Demi blush.

"What I thought if just I did it quick it wouldn't hurt as long," Demi said.

"But when I opened my eyes and looked up and saw Demi's eyes and felt all the love between her and me the pain went away," Mikayla said.

"Yeah the same with me it hurt at first but once I relaxed and looked into Mik's eyes the pain went away," Demi said. "Wait you do love Lilly right?," she continued

"Yeah of course I do she's the most beautiful girl I ever met I mean I see a future with her. I've never felt this way about anyone," Miley said.

"Well kid its just a matter of us getting out of here," David said coming from the other room. "So girls where we going," he asked wiping his glasses.

"Lets go to _Colors," _Demi said enthusiastically.

"No, no, no, any gay or straight club but colors please," David said with a sigh.

"Oh what's the matter big bro scared you gonna run into your boy friend" Mikayla said making everyone laugh but David.

"Not funny tiny Texan, and besides ya'll know I don't get down like that, and even if I did I'd like to think I could do better than that Jake Ryan guy," David said in an offended tone.

"So you remember his name. I don't know sounds like a love connection to me Davie," Miley said joining in teasing of her friend.

"Oh shut up Miley. Anyway why don't we hit Roma's for some pizza the lets go to _Heart_ _Breakers_ its amateur night Maybe Demi can show of some of those skills of hers," David getting a pillow thrown at his face.

"First off I am not an amateur and I only dance in public if I need the extra cash,"

"Yeah, yeah lets go," David said as the trio left the apartment.

"_Ok Miley you got about an hour to hit the shower and get everything set up," _Miley thought as she took her cover alls the rest of the way off and headed to the bathroom.

Thirty minutes later Miley found herself dressed in a pair of jeans and a simple wife beater, setting out the Chinese food she had ordered for herself and Lilly. As she was about to finish she herd a knock at the door that set about butterflies in her stomach. "Just a sec Lil, ," Miley said as she very quickly dimmed the lights in the apartment and turned on the stereo thankful that one of the many slow jam mix Cd's was still inside. As she walked to the door she did a quick breath check before opening it. Miley's mouth almost hit the floor at what she saw. There was Lilly looking as what Miley thought very definition sexy in her pink short, shorts and pink and black Dickies t-shirt holding her motorcycle helmet.

"Well sexy are you just going to stand there are or you going to let me in," Lilly said.

"Yeah shawty come on in babes," Miley said as she motioned the blonde girl in while thinking "_Damn why'd she'd have to wear those shorts."_

Lilly took in the atmosphere of the apartment and smiled to her self before saying "You know Miley Ray, the way the apartment's decked out somebody may think you have something planned."

"I might you know how I do," Miley with a raised eyebrow walking up behind Lilly

"Well in that why don't we skip dinner and just go straight to desert ," Lilly said in a seductive voice pushed Miley onto the couch. She then startled Miley's lap and began passionately kissing her. Soon Miley becoming swept up in lust and love for the blonde sitting atop her gently bit Lilly's lip making them part enough for Miley slip her tongue into her mouth. as the kiss deepened the two tongues began the blissful dance that both young women loved. They both often said that kissing the other felt like walking in heaven, a feeling neither of them felt with any other girl. As Lilly began to shift her kisses to her neck Miley saw she needed to stop things for a moment before things went to far.

"Lilly baby stop," Miley said making Lilly's beautiful eyes lock with hers.

"Miley what's wrong" Lilly asked

"Nothing's wrong Lilly-bear I just wanted to know something," Miley said.

"What?" Lilly asked.

"You love me right. I mean like if I slipped into a coma tomorrow you'd wait for me to come out of it," Miley asked the nervousness in her voice becoming apparent.

"Of course I would Miley. I mean I its only been four months but I've never loved anybody as much as I do you. You make me feel so alive inside and out. and I'll always love you no matter what," Lilly said sincerely.

"Are you sure Lilly," Miley asked.

"Yes baby I do," Lilly said placing a gentle kiss on Miley's forehead.

"Good baby cause I feel the same way tonight I wanted do something special tonight," Miley said nervously.

Lilly gave Miley a curious look and asked, "Special? Oh does somebody want to play quarter back and the bad cheerleader again," Lilly said with sexy smile in reference to one of there favorite bedroom games.

"No baby. Lilly I love you and I want you to ... ," Miley said pausing trying to find the right words as the butterflies in her stomach made them hard to find. "I want you to be the boy! I mean I want you to use my "sidekick" " Miley blurted out making herself blush.

"Are you sure Miley I mean this is one of things you can only do once ," Lilly asked. Lilly knew that in a sense Miley was still a virgin, and that in her past relationships Miley had always been in the male role when it came this aspect of love making. Lilly herself in her past relationships with women and her one relationship with guy had always been in the female role or has simply took turns being the dominant partner sexually. But she herself had never used a strap-on. Lilly also knew the level of trust that Miley was putting in her a trust she hoped she was fully worthy of.

"Lilly I've never felt this way about any other girl. You make me feel superhuman fearless Lilly. I have never felt this loved by a woman since my mom died, you're the one Lilly," Miley said with a tear in her eyes. Lilly then kissed the tears away and then began to focus on her lips and once again their tongues began their dance. Soon hands began to roam and both girls found themselves topless on the couch.

"Oh Miley," Lilly moaned as Miley's lips found her harden nipple. " Baby I think its time to go to the bedroom," Lilly said with a hitched voice.

"I think you're right," Miley grabbed Lilly's thighs and stood while for her part Lilly locked her legs around Miley's waist neither girl wanting to break the contact as they made their way to the bedroom

Miley and Lilly slung each other onto the bed and both girls quickly removed the last of their clothing not caring where the articles landed as they fondled each others bodies. A chorus of heavy panting and moans filled the room as the girls grinded aginst each other. "Oh Lilly Im so wet for you baby," Miley moaned as Lilly rolled her onto her back and began to tease her clit. Lilly then forcefully kissed Miley feed the heady lust between the girls. Lilly then ran her finger teasinly up the wet folds of Miley's sex and broke the kiss and teasingly licked the wetness off

"Are you ready baby?" Lilly asked with a sedutive smirk getting a nod from Miley. "Where is it?"she asked in refrence to the strap-on

"In the night stand top drawer," Miley said the pasion and love she felt for Lilly over riding her nerves. Lilly slid of the bed and wlked over to Miley's night stand and retrived the eight inch red strap-on with a vibrating harness. Miley saw Lilly look akward at the sex toy and asked, "Baby do you need me to um you know help you put it on."

Lilly's face turned bright pink and her lips formed an akward child like smile , before saying "Yeah I kinda do," in a bashfull tone.

Miley stood from the bed and motioned Lilly to her and told her to bring the small bottle of lube that was also in the drawer. Once Lilly was in front oher Miley took the toy and kissed her deeply and told her it was ok to be nervous. she then slowly lowered herself to her knees and kissed began to place butterfly kisses one Lilly's stomach making the blonde shutter while she secured the strap-on in place ariund Lilly's waist while at the same time teasly rubbing her sex. Miley then stood again and took the lube and squrited a small amount in into her hand and began to pump her hand up and down the length of the faux member. As she did she again felt the butterfiles stiring.

Lilly seeing this cupped Miley's cheek and kissed the slighty masculine girl and asked," Are you still sure about this Miley,"

"Yeah just go slow and be gentle please," Miley said, And with that the two embraced in a heated kiss. Miley soon found herself on her back with Lilly on top of her. She could feel the head of the strap-on rub against her pubic mound and she instintivly spread her legs allowing Lilly full access to her sex. Lilly taking the que propped her self up on her knees and placed the tip at Miley's entrance. She then slowly began to lower body onto Miley's She then heard Miley let out a sharp gasp and felt her tense and saw a few tear drops flow from her eyes making her stop.

"Baby are you ok," Lilly asked with a concerned voice

Miley felt the sharp pain tare through her body and knew that Lilly had taken her virginity. Through the pain she now felt she opened her eyes and saw the beautiful ocean blue eyes of Lilly looking down at her, and at that moment all the pain she felt was replaced by love and passion. "Im good baby just keep going," and with that Lilly began to slowly move herself in and out of Miley. Both soon began to feel the arusol and lust with in them grow lick the heat in a valcano. "Lilly I love you baby," Miley hissed as the pace of Lilly's strokes increassed.

"Love you too baby," Lilly moaned as the vibrating nub inside the harness pressed againist her clit

"Go deeper baby," Moaned feeling her lust take over "OH DAMN BABYGIRL RIGHT THERE" she screamed as Lilly hit her G- spot

"Yeah you like that baby, does momma like how babygirl does it? Does it feel good Miley," Lilly grunted lustfully as as she fell into her roll as the domnant partner.

"YEESS IT FEELS GOOD OH GOD ITS SO GOOD," Miley whaled as locked her legs around Lilly.

Lilly could tell that the thrill of the new exprience was bringing about Miley's climax sooner than expect in effort to share the expirence Lilly increased the speed of her thrust. " OH SAY MY NAME MILEY! SAY NAME I LOVE IT WHEN YOU SAY IT!"

"LIL....LIL LILLLYY! OH LILLY!," Miley stutter yelled as Lilly drove into her "OH LILLY BABY I'M ABOUT TO CUMM," she moaned as her impendig orgasm was moments away.

"OH CUUM MILEY! WITH ME!" Lilly said as she too was about reach her peak. The next few all that could be heard where moan and heavy breathing as both girls reach a shared orgasmic high. Lilly rolled off of Miley and layed her head marvel in silence as she listen to the heart the beat in time with hers

**A/N: I know short right but somtimes things can be short annd say it all anyway hope you enjoyeed it. Oh and before I go I want you to know those of you read my Tomboy Liley fic Wonderland TV still have time to get your questions in for the next chapter the rules are in the last chapter anyway Peace and blessings and remember reviews are love**


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